NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1167.68
Volume:	1188.708
LogP:	4.397
LogD:	3.363
LogS:	-2.587
# Rotatable Bonds:	30
TPSA:	351.34
# H-Bond Aceptor:	24
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.028
Synthetic Accessibility Score:	6.966
Fsp3:	0.712
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.128
MDCK Permeability:	0.0001850677072070539
Pgp-inhibitor:	0.895
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.789
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.893

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.171
Plasma Protein Binding (PPB):	46.114158630371094%
Volume Distribution (VD):	0.777
Pgp-substrate:	37.56498718261719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.047

ADMET: Excretion

Clearance (CL):	1.261
Half-life (T1/2):	0.716

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.073
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.491

Download Data

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General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476978

Natural Product ID:	NPC476978
*Common Name:**	Mebamamide A
IUPAC Name:	[(3S,8R)-10-[[(2R)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-[[(3R,6S,7R,10S,13R,16S)-3-benzyl-7-methyl-13-(2-methylpropyl)-2,5,9,12,15-pentaoxo-10-propan-2-yl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]amino]-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-8-hydroxy-2-methyl-10-oxodecan-3-yl] acetate
Synonyms:
Standard InCHIKey:	SNUSGYYFKHRIQF-PTYJSHCWSA-N
Standard InCHI:	InChI=1S/C59H93N9O15/c1-32(2)27-41-52(74)65-49(35(7)8)59(81)82-37(10)50(56(78)64-43(29-39-19-13-12-14-20-39)58(80)68-26-18-23-46(68)55(77)62-41)66-51(73)36(9)60-54(76)45-22-17-25-67(45)57(79)42(28-33(3)4)63-53(75)44(31-69)61-48(72)30-40(71)21-15-16-24-47(34(5)6)83-38(11)70/h12-14,19-20,32-37,40-47,49-50,69,71H,15-18,21-31H2,1-11H3,(H,60,76)(H,61,72)(H,62,77)(H,63,75)(H,64,78)(H,65,74)(H,66,73)/t36-,37-,40-,41-,42+,43-,44-,45+,46+,47+,49+,50+/m1/s1
SMILES:	C[C@@H]1[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N[C@H](C(=O)O1)C(C)C)CC(C)C)CC3=CC=CC=C3)NC(=O)[C@@H](C)NC(=O)[C@@H]4CCCN4C(=O)[C@H](CC(C)C)NC(=O)[C@@H](CO)NC(=O)C[C@@H](CCCC[C@@H](C(C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122178814
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33689	Derbesia marina	Species	Derbesiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25768725]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	19000	nM	PMID[25768725]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	48000	nM	PMID[25768725]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476978 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	669
0.2-0.3	2357
0.3-0.4	16980
0.4-0.5	18192
0.5-0.6	3371
0.6-0.7	582
0.7-0.8	263
0.8-0.85	70
0.85-0.9	72
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9203	High Similarity	NPC5620
0.9078	High Similarity	NPC2501
0.8963	High Similarity	NPC287401
0.8955	High Similarity	NPC130309
0.8944	High Similarity	NPC129666
0.8921	High Similarity	NPC161069
0.8905	High Similarity	NPC471265
0.8905	High Similarity	NPC471264
0.8889	High Similarity	NPC122590
0.8873	High Similarity	NPC240848
0.8865	High Similarity	NPC314358
0.8865	High Similarity	NPC262077
0.8849	High Similarity	NPC263493
0.8849	High Similarity	NPC269398
0.8841	High Similarity	NPC92784
0.8841	High Similarity	NPC476133
0.8841	High Similarity	NPC98424
0.8841	High Similarity	NPC470884
0.8841	High Similarity	NPC178662
0.8794	High Similarity	NPC313867
0.8794	High Similarity	NPC316008
0.8794	High Similarity	NPC209509
0.8777	High Similarity	NPC239762
0.8777	High Similarity	NPC163392
0.8776	High Similarity	NPC197743
0.8776	High Similarity	NPC297145
0.8723	High Similarity	NPC315283
0.8723	High Similarity	NPC314388
0.8723	High Similarity	NPC52748
0.8712	High Similarity	NPC6975
0.8712	High Similarity	NPC46427
0.869	High Similarity	NPC162104
0.8671	High Similarity	NPC225648
0.8671	High Similarity	NPC138775
0.8671	High Similarity	NPC329761
0.8636	High Similarity	NPC252878
0.8621	High Similarity	NPC475168
0.8621	High Similarity	NPC7817
0.8611	High Similarity	NPC471820
0.8611	High Similarity	NPC471821
0.8561	High Similarity	NPC202521
0.8531	High Similarity	NPC315266
0.8521	High Similarity	NPC139326
0.8511	High Similarity	NPC46098
0.8511	High Similarity	NPC268841
0.8511	High Similarity	NPC307357
0.8485	Intermediate Similarity	NPC200964
0.8485	Intermediate Similarity	NPC476990
0.8462	Intermediate Similarity	NPC477462
0.8446	Intermediate Similarity	NPC470902
0.8414	Intermediate Similarity	NPC145113
0.8414	Intermediate Similarity	NPC135121
0.8406	Intermediate Similarity	NPC255447
0.8369	Intermediate Similarity	NPC68865
0.8357	Intermediate Similarity	NPC248283
0.8333	Intermediate Similarity	NPC310467
0.8333	Intermediate Similarity	NPC200589
0.8321	Intermediate Similarity	NPC319766
0.8276	Intermediate Similarity	NPC201244
0.8276	Intermediate Similarity	NPC477217
0.8264	Intermediate Similarity	NPC197682
0.8264	Intermediate Similarity	NPC77905
0.8258	Intermediate Similarity	NPC169328
0.8239	Intermediate Similarity	NPC127741
0.8227	Intermediate Similarity	NPC141050
0.8194	Intermediate Similarity	NPC168113
0.8176	Intermediate Similarity	NPC283783
0.817	Intermediate Similarity	NPC469901
0.8138	Intermediate Similarity	NPC176226
0.8133	Intermediate Similarity	NPC473341
0.8125	Intermediate Similarity	NPC476259
0.8113	Intermediate Similarity	NPC26108
0.8108	Intermediate Similarity	NPC105717
0.8071	Intermediate Similarity	NPC300315
0.8069	Intermediate Similarity	NPC469427
0.8069	Intermediate Similarity	NPC469426
0.805	Intermediate Similarity	NPC137627
0.8029	Intermediate Similarity	NPC175726
0.8029	Intermediate Similarity	NPC474082
0.8027	Intermediate Similarity	NPC322878
0.8026	Intermediate Similarity	NPC469903
0.8013	Intermediate Similarity	NPC472923
0.8013	Intermediate Similarity	NPC262166
0.8	Intermediate Similarity	NPC473322
0.7987	Intermediate Similarity	NPC62104
0.7987	Intermediate Similarity	NPC1390
0.7958	Intermediate Similarity	NPC246079
0.7949	Intermediate Similarity	NPC471052
0.7949	Intermediate Similarity	NPC471053
0.7949	Intermediate Similarity	NPC471051
0.7941	Intermediate Similarity	NPC478015
0.7941	Intermediate Similarity	NPC478014
0.7941	Intermediate Similarity	NPC478016
0.7935	Intermediate Similarity	NPC471527
0.7926	Intermediate Similarity	NPC470546
0.7925	Intermediate Similarity	NPC475204
0.7925	Intermediate Similarity	NPC475123
0.7914	Intermediate Similarity	NPC101719
0.7895	Intermediate Similarity	NPC286551
0.7895	Intermediate Similarity	NPC202198
0.7888	Intermediate Similarity	NPC317362
0.7888	Intermediate Similarity	NPC318930
0.7871	Intermediate Similarity	NPC469898
0.7862	Intermediate Similarity	NPC473000
0.7852	Intermediate Similarity	NPC470545
0.7842	Intermediate Similarity	NPC222466
0.784	Intermediate Similarity	NPC469900
0.7821	Intermediate Similarity	NPC469902
0.781	Intermediate Similarity	NPC45777
0.781	Intermediate Similarity	NPC477061
0.781	Intermediate Similarity	NPC190663
0.7806	Intermediate Similarity	NPC324850
0.7794	Intermediate Similarity	NPC237420
0.7785	Intermediate Similarity	NPC217804
0.7785	Intermediate Similarity	NPC210377
0.7785	Intermediate Similarity	NPC5719
0.7785	Intermediate Similarity	NPC22883
0.7778	Intermediate Similarity	NPC315276
0.7778	Intermediate Similarity	NPC14672
0.7778	Intermediate Similarity	NPC471165
0.7778	Intermediate Similarity	NPC285926
0.7778	Intermediate Similarity	NPC470544
0.7746	Intermediate Similarity	NPC111428
0.7716	Intermediate Similarity	NPC306804
0.7711	Intermediate Similarity	NPC167763
0.7711	Intermediate Similarity	NPC470903
0.7711	Intermediate Similarity	NPC470112
0.7698	Intermediate Similarity	NPC160493
0.7688	Intermediate Similarity	NPC63040
0.7688	Intermediate Similarity	NPC302597
0.7687	Intermediate Similarity	NPC132636
0.7687	Intermediate Similarity	NPC89489
0.7676	Intermediate Similarity	NPC71933
0.7676	Intermediate Similarity	NPC89923
0.7676	Intermediate Similarity	NPC152850
0.7676	Intermediate Similarity	NPC105114
0.7676	Intermediate Similarity	NPC239990
0.7669	Intermediate Similarity	NPC326407
0.7669	Intermediate Similarity	NPC279871
0.7669	Intermediate Similarity	NPC317725
0.7662	Intermediate Similarity	NPC261934
0.7662	Intermediate Similarity	NPC56685
0.7662	Intermediate Similarity	NPC5194
0.766	Intermediate Similarity	NPC47667
0.763	Intermediate Similarity	NPC33742
0.7625	Intermediate Similarity	NPC15068
0.7606	Intermediate Similarity	NPC136453
0.7593	Intermediate Similarity	NPC46009
0.7578	Intermediate Similarity	NPC107938
0.7578	Intermediate Similarity	NPC294516
0.7566	Intermediate Similarity	NPC16188
0.7561	Intermediate Similarity	NPC155506
0.7561	Intermediate Similarity	NPC159767
0.7561	Intermediate Similarity	NPC476227
0.7561	Intermediate Similarity	NPC136797
0.7556	Intermediate Similarity	NPC35850
0.7556	Intermediate Similarity	NPC276949
0.7554	Intermediate Similarity	NPC80150
0.7547	Intermediate Similarity	NPC241794
0.7546	Intermediate Similarity	NPC230611
0.7546	Intermediate Similarity	NPC328494
0.7546	Intermediate Similarity	NPC89831
0.7531	Intermediate Similarity	NPC469904
0.753	Intermediate Similarity	NPC269750
0.753	Intermediate Similarity	NPC194671
0.753	Intermediate Similarity	NPC475421
0.7518	Intermediate Similarity	NPC239357
0.7517	Intermediate Similarity	NPC157311
0.75	Intermediate Similarity	NPC473002
0.75	Intermediate Similarity	NPC81026
0.7485	Intermediate Similarity	NPC196091
0.7485	Intermediate Similarity	NPC40234
0.7484	Intermediate Similarity	NPC473003
0.7484	Intermediate Similarity	NPC300443
0.7466	Intermediate Similarity	NPC8761
0.7466	Intermediate Similarity	NPC44805
0.7455	Intermediate Similarity	NPC473402
0.7453	Intermediate Similarity	NPC63931
0.7438	Intermediate Similarity	NPC73655
0.7434	Intermediate Similarity	NPC266741
0.7434	Intermediate Similarity	NPC471680
0.7419	Intermediate Similarity	NPC473491
0.741	Intermediate Similarity	NPC50016
0.7394	Intermediate Similarity	NPC273755
0.7389	Intermediate Similarity	NPC39431
0.7381	Intermediate Similarity	NPC472999
0.7376	Intermediate Similarity	NPC71684
0.7362	Intermediate Similarity	NPC473502
0.7362	Intermediate Similarity	NPC141957
0.7353	Intermediate Similarity	NPC474584
0.7353	Intermediate Similarity	NPC294951
0.7353	Intermediate Similarity	NPC273814
0.7349	Intermediate Similarity	NPC473354
0.7343	Intermediate Similarity	NPC22746
0.7342	Intermediate Similarity	NPC244509
0.7338	Intermediate Similarity	NPC311658
0.7329	Intermediate Similarity	NPC69496
0.7326	Intermediate Similarity	NPC4910
0.7324	Intermediate Similarity	NPC317474
0.7324	Intermediate Similarity	NPC291027

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	317
0.2-0.3	630
0.3-0.4	2257
0.4-0.5	3875
0.5-0.6	1571
0.6-0.7	302
0.7-0.8	92
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8905	High Similarity	NPD8173	Phase 2
0.8905	High Similarity	NPD8172	Phase 2
0.8571	High Similarity	NPD2584	Suspended
0.8298	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD8416	Discontinued
0.8163	Intermediate Similarity	NPD8323	Discontinued
0.8	Intermediate Similarity	NPD4175	Approved
0.8	Intermediate Similarity	NPD4177	Approved
0.7986	Intermediate Similarity	NPD5725	Approved
0.7943	Intermediate Similarity	NPD4125	Approved
0.7917	Intermediate Similarity	NPD8643	Discontinued
0.7862	Intermediate Similarity	NPD6073	Approved
0.7857	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5747	Discontinued
0.7778	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD8076	Discontinued
0.7643	Intermediate Similarity	NPD3073	Approved
0.7643	Intermediate Similarity	NPD3072	Approved
0.7643	Intermediate Similarity	NPD3071	Approved
0.7607	Intermediate Similarity	NPD8124	Phase 3
0.7607	Intermediate Similarity	NPD7964	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7965	Phase 2
0.7607	Intermediate Similarity	NPD8126	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4761	Approved
0.7571	Intermediate Similarity	NPD4762	Approved
0.7569	Intermediate Similarity	NPD4676	Approved
0.7569	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6852	Discontinued
0.7568	Intermediate Similarity	NPD6901	Phase 3
0.7552	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5264	Approved
0.755	Intermediate Similarity	NPD5265	Approved
0.7517	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7613	Discontinued
0.7483	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4153	Approved
0.7448	Intermediate Similarity	NPD5263	Approved
0.7405	Intermediate Similarity	NPD8417	Discontinued
0.7397	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4738	Phase 2
0.7379	Intermediate Similarity	NPD3626	Phase 3
0.7375	Intermediate Similarity	NPD4557	Approved
0.7365	Intermediate Similarity	NPD6623	Phase 3
0.7355	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7512	Approved
0.7351	Intermediate Similarity	NPD7511	Approved
0.7329	Intermediate Similarity	NPD2613	Approved
0.7324	Intermediate Similarity	NPD2608	Approved
0.7324	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4215	Approved
0.7324	Intermediate Similarity	NPD2611	Approved
0.7324	Intermediate Similarity	NPD3131	Approved
0.7324	Intermediate Similarity	NPD2610	Approved
0.7324	Intermediate Similarity	NPD2609	Approved
0.7324	Intermediate Similarity	NPD4217	Approved
0.7324	Intermediate Similarity	NPD4218	Approved
0.7324	Intermediate Similarity	NPD3132	Approved
0.7324	Intermediate Similarity	NPD2612	Approved
0.7324	Intermediate Similarity	NPD4216	Approved
0.7297	Intermediate Similarity	NPD3614	Approved
0.7297	Intermediate Similarity	NPD3615	Approved
0.7297	Intermediate Similarity	NPD2566	Approved
0.7297	Intermediate Similarity	NPD3090	Approved
0.7297	Intermediate Similarity	NPD3087	Approved
0.7297	Intermediate Similarity	NPD3089	Approved
0.7297	Intermediate Similarity	NPD4745	Approved
0.7297	Intermediate Similarity	NPD2571	Approved
0.7297	Intermediate Similarity	NPD2570	Approved
0.7297	Intermediate Similarity	NPD2573	Approved
0.7297	Intermediate Similarity	NPD3616	Approved
0.7297	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2574	Discontinued
0.7297	Intermediate Similarity	NPD3088	Approved
0.7297	Intermediate Similarity	NPD4746	Phase 3
0.7296	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5759	Approved
0.7255	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2437	Approved
0.7255	Intermediate Similarity	NPD2436	Approved
0.7248	Intermediate Similarity	NPD5296	Approved
0.7244	Intermediate Similarity	NPD6088	Approved
0.723	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4126	Approved
0.72	Intermediate Similarity	NPD4686	Approved
0.72	Intermediate Similarity	NPD4685	Phase 3
0.72	Intermediate Similarity	NPD4684	Phase 3
0.7195	Intermediate Similarity	NPD8303	Discontinued
0.7192	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3588	Discontinued
0.7172	Intermediate Similarity	NPD6792	Phase 3
0.717	Intermediate Similarity	NPD8315	Phase 1
0.7163	Intermediate Similarity	NPD2217	Approved
0.7163	Intermediate Similarity	NPD2218	Phase 2
0.7162	Intermediate Similarity	NPD4794	Discontinued
0.7152	Intermediate Similarity	NPD7510	Approved
0.7143	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3040	Approved
0.7133	Intermediate Similarity	NPD8265	Approved
0.7114	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1330	Phase 2
0.7105	Intermediate Similarity	NPD6294	Approved
0.7105	Intermediate Similarity	NPD6295	Approved
0.7103	Intermediate Similarity	NPD4677	Discontinued
0.708	Intermediate Similarity	NPD3644	Approved
0.708	Intermediate Similarity	NPD3643	Approved
0.708	Intermediate Similarity	NPD3642	Approved
0.7078	Intermediate Similarity	NPD2022	Approved
0.7071	Intermediate Similarity	NPD1348	Approved
0.707	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4647	Approved
0.7063	Intermediate Similarity	NPD4646	Approved
0.7063	Intermediate Similarity	NPD4648	Approved
0.7059	Intermediate Similarity	NPD3480	Approved
0.7055	Intermediate Similarity	NPD7599	Phase 2
0.7055	Intermediate Similarity	NPD3125	Approved
0.7047	Intermediate Similarity	NPD2051	Approved
0.7047	Intermediate Similarity	NPD21	Approved
0.7047	Intermediate Similarity	NPD2048	Approved
0.7047	Intermediate Similarity	NPD2043	Approved
0.7047	Intermediate Similarity	NPD2047	Approved
0.7047	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2045	Approved
0.7047	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2046	Approved
0.7047	Intermediate Similarity	NPD2044	Approved
0.7032	Intermediate Similarity	NPD6681	Discovery
0.702	Intermediate Similarity	NPD5323	Approved
0.7012	Intermediate Similarity	NPD7600	Phase 2
0.7	Intermediate Similarity	NPD4619	Approved
0.7	Intermediate Similarity	NPD4621	Approved
0.7	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5981	Approved
0.6983	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8351	Phase 2
0.6968	Remote Similarity	NPD7720	Phase 2
0.6968	Remote Similarity	NPD2087	Approved
0.6968	Remote Similarity	NPD4152	Approved
0.6968	Remote Similarity	NPD2088	Approved
0.6954	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5367	Discontinued
0.6937	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5230	Approved
0.6937	Remote Similarity	NPD5229	Approved
0.6929	Remote Similarity	NPD2652	Approved
0.6929	Remote Similarity	NPD2650	Approved
0.6929	Remote Similarity	NPD3598	Phase 3
0.6923	Remote Similarity	NPD6343	Approved
0.6923	Remote Similarity	NPD6345	Approved
0.6918	Remote Similarity	NPD3988	Approved
0.6918	Remote Similarity	NPD3987	Approved
0.6913	Remote Similarity	NPD3661	Approved
0.6913	Remote Similarity	NPD3663	Approved
0.6913	Remote Similarity	NPD3662	Phase 3
0.6913	Remote Similarity	NPD3664	Approved
0.6905	Remote Similarity	NPD6303	Approved
0.6905	Remote Similarity	NPD6304	Approved
0.6899	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7011	Discontinued
0.6887	Remote Similarity	NPD5299	Approved
0.6863	Remote Similarity	NPD3908	Approved
0.6853	Remote Similarity	NPD7522	Discontinued
0.6852	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4567	Approved
0.6848	Remote Similarity	NPD4566	Approved
0.6846	Remote Similarity	NPD4151	Approved
0.6839	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7342	Discontinued
0.6815	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5613	Approved
0.6813	Remote Similarity	NPD5614	Approved
0.6795	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7131	Phase 3
0.6788	Remote Similarity	NPD7130	Phase 3
0.6783	Remote Similarity	NPD4574	Approved
0.6783	Remote Similarity	NPD3123	Discovery
0.6783	Remote Similarity	NPD4576	Approved
0.6779	Remote Similarity	NPD2159	Approved
0.6779	Remote Similarity	NPD2625	Approved
0.6779	Remote Similarity	NPD2626	Approved
0.6779	Remote Similarity	NPD2628	Approved
0.6779	Remote Similarity	NPD2160	Approved
0.6779	Remote Similarity	NPD2627	Approved
0.6776	Remote Similarity	NPD5581	Approved
0.6761	Remote Similarity	NPD747	Discontinued
0.6746	Remote Similarity	NPD4508	Discontinued
0.6736	Remote Similarity	NPD2116	Approved
0.6736	Remote Similarity	NPD5990	Approved
0.6736	Remote Similarity	NPD2117	Pre-registration
0.6736	Remote Similarity	NPD2115	Approved
0.6736	Remote Similarity	NPD6065	Approved
0.6736	Remote Similarity	NPD5991	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data